Haven't played this in a long time, decided this was a good chance to go through it and catch up with the latest update. It has been long enough that I've currently around $7,500 cash lying around.
Tara has two main and one side quest remaining. Roommate has been at 4) She's at her wits end, a few more days of waiting should conclude the thing, and has been there for weeks, no idea if there is a trigger to conclude this or not. Lies is on 17) and I suspect this requires progress with Shego.
Bonnie is complete, for what it is worth, I would suggest turning one her CAAB walks into repeatable content since you'll spend a lot of time waiting for stuff.
Misc Whereisit 8) I'll ask her to come in on Friday never resolved, but neither Kim nor Monique has a normal option to come to work on Friday specifically, so I'm assuming that this is simply something which resolved but didn't update the quest list.
Ann is on Couldhavebeen 16) Call Junior, and this is a problem.
Shego Bluffing appears to be the issue, because I'm on 15) where I need to mess with her on evenings, after she's had to endure a day. I've tried talking and sex options on weekdays and weekend evenings, to no avail. I apparently can't talk to Junior until this is complete, it isn't completing. I do not know if this is just unfortunate timing with the demand to call Junior over Ann, which I find much more interesting, or if these were intended to be locked together, but this is quite frustrating.
There is remaining content, all of which appears to be trapped behind progress with Tara and Shego, which isn't happening. I'll keep playing for a bit, but I don't know what else to try.